S$ 586 Find Cheap Flights from Chicago to Singapore

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 7-9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Singapore

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Singapore that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Singapore

Fri, 11 Sep - Fri, 25 Sep
Delta Logo
06:00 - 23:55
MDW
-
SIN
28h 55m
2 stops
Delta Logo
22:00 - 15:35
SIN
-
MDW
30h 35m
2 stops
S$ 1,524Delta
Sun, 9 Aug - Mon, 24 Aug
Air Canada Logo
14:15 - 05:15
ORD
-
SIN
26h 00m
2 stops
Air Canada Logo
06:15 - 20:05
SIN
-
ORD
26h 50m
2 stops
S$ 1,526Air Canada
Fri, 3 Jul - Mon, 13 Jul
United Airlines Logo
07:30 - 18:35
ORD
-
SIN
22h 05m
1 stop
United Airlines Logo
20:35 - 05:57
SIN
-
ORD
22h 22m
1 stop
S$ 1,538United Airlines
Wed, 1 Jul - Sat, 4 Jul
United Airlines Logo
06:10 - 06:15
ORD
-
SIN
35h 05m
1 stop
United Airlines Logo
08:45 - 21:38
SIN
-
ORD
25h 53m
1 stop
S$ 1,549United Airlines
Thu, 9 Jul - Thu, 16 Jul
Air Canada Logo
08:45 - 00:45
ORD
-
SIN
27h 00m
2 stops
Air Canada Logo
07:00 - 13:07
SIN
-
ORD
43h 07m
2 stops
S$ 1,551Air Canada
Tue, 30 Jun - Fri, 3 Jul
United Airlines Logo
06:10 - 18:35
ORD
-
SIN
23h 25m
1 stop
United Airlines Logo
11:05 - 23:22
SIN
-
ORD
25h 17m
2 stops
S$ 1,552United Airlines
Thu, 2 Jul - Sun, 5 Jul
United Airlines Logo
06:00 - 00:45
ORD
-
SIN
29h 45m
2 stops
United Airlines Logo
20:35 - 07:16
SIN
-
ORD
23h 41m
1 stop
S$ 1,553United Airlines
Fri, 14 Aug - Sat, 22 Aug
Delta Logo
06:05 - 23:55
MDW
-
SIN
28h 50m
2 stops
Delta Logo
22:00 - 16:15
SIN
-
MDW
31h 15m
2 stops
S$ 1,555Delta
Sat, 8 Aug - Sat, 15 Aug
Delta Logo
05:30 - 23:55
ORD
-
SIN
29h 25m
2 stops
Delta Logo
22:00 - 14:09
SIN
-
ORD
29h 09m
2 stops
S$ 1,555Delta
Fri, 21 Aug - Wed, 9 Sep
Japan Airlines Logo
10:40 - 00:20
ORD
-
SIN
24h 40m
1 stop
Japan Airlines Logo
08:05 - 00:30
SIN
-
ORD
29h 25m
2 stops
S$ 1,557Japan Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly, and much more.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Singapore is January, when tickets cost S$ 633 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of return tickets is S$ 1,253 and S$ 1,086 respectively.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on the flight from Chicago to Singapore, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 1 week before departure.

Good to know

Low seasonApril
Cheapest flightS$ 586
Best time to beat the crowds (23% less expensive on average)
Most popular time to fly (74% more expensive on average)
Flight from Chicago O'Hare Airport to Singapore

FAQs - booking Singapore flights

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Singapore is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to Singapore with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Singapore?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Singapore

 
Need help choosing which airline to fly with from Chicago to Singapore? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
Etihad AirwaysOverall score based on 1452 reviews
7.6Boarding
7.3Comfort
7.8Crew
7.2Entertainment
7.2Food
Airline reviews

i have book the flight with baggage. and i have paid $800.00 for the baggage. when i contacted to JUSTFLY Costumer Service they told me that my baggage was included in the booking. then why i have to pay. i am going to file a complain against it. $800.00 is not at all small amount

2.0 MediocreAnonymous, Jun 2026
ATL - AUH
Read more Etihad Airways reviews

i have book the flight with baggage. and i have paid $800.00 for the baggage. when i contacted to JUSTFLY Costumer Service they told me that my baggage was included in the booking. then why i have to pay. i am going to file a complain against it. $800.00 is not at all small amount

They lost the baggage and said it was deleted from the system. I had baggage tag so was able to file the complaint but there was no PIR number and update so far

Very disappointed to not have lounge access The shorter flight seats were uncomfortable

Seats were very comfortable and the staff too was very friendly.

1 hour delay meant missed my connecting flight and 1st day of holiday

Dear Team, I purchased a full travel package that included 2 checked bags through you and JustFly. However, when I arrived at the airport, my ticket showed 0 checked bags. Since I was traveling internationally to India with 2 bags, It was a $200 per bag at the counter, which was extremely disappointing. For an international trip, why would I ever choose a no‑bag option for only $20–$30 less? This seems like an error in the booking process, and I am requesting clarification and a resolution. I have called JustFly and on phone for 1 hr :53 min and they couldn't help till I show some kind of proof etc which isn't possible but besides that love your service and using it for years !

Good one but just notice that you have to ask several time to get water or coffee .

The flight was over 1 hour late taking off ,when I arrived in Abu Dhabi ,I missed my connecting flight to Bangkok so I had to wait almost 6 hours for my flight arriving in Bangkok at 6:30 am ,So I missed a whole day of my vacation and my hotel room sat empty so I paid for hotel days that I was not there. In Abu Dhabi there was a woman that worked the desk at transfers that was so professional, courteous , helpful,and may I say absolutely beautiful .she got me food vouchers for my layover and was a very calming presence. Besides that I will never use Etihad again I will pay the Xtra money . I'm sure they won't read or see this but it's my "2 cents" I'll use an airline that respects me and my hard earned dollars

I booked and paid for a Business Class seat for myself and my wife. 4 hours before the flight i get a call saying the plane they sent doesn't have the correct layout to accommodate all the business class seats they sold me 3 months earlier at a premium of $1500 a ticket. So they have to bump me from Business to Economy and will give me a $400 credit (total of $800 for both seats) that I could turn in at Abu Dahbi for $400 in US cash. They then promised a row that we could have to ourselves and the arm rests would go up so we could spread out for each of us. My wife was taken care of but I was put in the exit row with the flight attendents set as part of the three...and the arm rest did not go up. When we got to Abu Dahbi, they would not exchange our credit for cash as promised. Very disappointed they took my money 3 months ago and refused to reimburse for the change in seats or follow the promises made.

It was fantastic. The flight from Chicago to Abu Dahbi was fantastic. The crew, food and service were amazing. Everything was handled by the crew member assigned to us , Nicholas, was usually done before we asked for it. Highly recommend Etihad!

Everything you need to know for your flight from Chicago to Singapore

Cabin class types available on flights to Singapore

Cabin classes available on flights to Singapore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.